But the pathological gambling addict was actually preparing to go into custody, awaiting sentence for stealing more than $700,000 from his previous employer.
When his boss caught wind of the real story, he discovered Crowe had made unauthorised transactions from his business as well - to the tune of $1.6 million. He personally pocketed nearly $800,000 of that.
Crowe was jailed on Wednesday for six years after gambling away all the stolen funds. He must serve at least three-and-a-half years before he's eligible for parole.
His offending against Melbourne River Cruises began in September 2014, nearly a decade after he joined the company as a bookkeeper. He had been promoted to financial controller.
Crowe turned to cocaine and other substances after the breakdown of his marriage and saw gambling as a way to pay off a drug debt.
But his addiction spiralled and he gambled more and more to win back what he was stealing from the family-run business, through transfers to an account he called "petty cash".
In all he pocketed just shy of $712,000 before getting caught in February 2017. He lost his job and signed a letter promising to repay the funds but never did and in 2018 he was charged with theft.
In the meantime Crowe found another job with onQ Plumbing and Excavations as a bookkeeper.
Almost immediately he started stealing from them too.
Between December 2017 and September 2020 - including a period he was on bail and awaiting sentencing on two charges of theft from Melbourne River Cruises - Crowe transferred $1.6 million from onQ accounts to his own.
He began paying the plumbing company's creditors from his own personal accounts but was charged with obtaining property by deception over $791,586 that he kept for himself.
Crowe's deception was uncovered after he quit.
When his old bosses struggled to chase him up about a training manual he was supposed to leave for his replacement they read that he had faced court and been taken into custody for the thefts, prompting audits of their own books.
Crowe described himself as having an extensive gambling addiction, something Judge Allen said was correct, if not an understatement.
He was spending thousands of dollars a day betting on sport, had multiple online betting accounts and would visit Crown Casino multiple times daily.
Compulsive gambling meant he never had the funds to repay what he stole.
"I just kept digging myself in deeper," Crowe told a medical expert ahead of the sentencing.
He also pleaded guilty to attempting to pervert the course of justice after lying about giving up gambling ahead of a pre-sentence hearing.
"You attempted to deceive this court into imposing a sentence in this matter which you hoped would be less than that which you deserved," the judge said.
He found the father-of-five had good prospects for rehabilitation if he is treated for his gambling addiction.
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